


Why Can't This Be Real?

by JaredSamalecki



Series: Tumblr Prompts [27]
Category: Gilmore Girls
Genre: College, Cute, Drama, Exams, F/M, Fake/Pretend Relationship, Falling In Love, Fluff, Getting Together, Getting to Know Each Other, Idiots in Love, Moving In Together, One Shot, Reader-Insert, Studying, but they fall in love, dean forester is a good boyfriend, hand holding, imagine, just go with it, let's be honest the math and science is probably wrong, x Reader
Language: English
Status: Completed
Published: 2020-06-03
Updated: 2020-06-06
Packaged: 2021-03-04 04:47:13
Rating: General Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 6,470
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24527860
Author URL: https://archiveofourown.org/users/JaredSamalecki/pseuds/JaredSamalecki
Summary: Can you do a Dean Forester x reader fake dating au? Like after Dean and Rory broke up Jess broke up with the reader, then Rory started dating Jess and the reader and Dean were both really hurt, and they start fake dating to spite Rory and Jess (and give Stars hollow something to really gossip about) but things are going really well and they end up helping each other get full scholarships and at some point Dean is like "fuck it, I accidentally fell in love with u, can we date for real?"
Relationships: Dean Forester & Reader, Dean Forester/Reader, Dean Forester/Rory Gilmore, Jess Mariano/Reader, Previous Mentions of -, Rory Gilmore/Jess Mariano
Series: Tumblr Prompts [27]
Series URL: https://archiveofourown.org/series/1419061
Comments: 5
Kudos: 30





	1. Chapter 1

**Author's Note:**

> Want to request something? Leave a comment or head over to my tumblr. Prompt lists can be found in my bio at https://multi-fandom-imagines-x.tumblr.com/
> 
> Thanks for reading and stay safe everyone!

You had to admit that you weren’t all too shocked when Jess left you for Rory after the dramatic breakup between Rory and Dean. You were there to witness Dean finally lose his temper and snap, you couldn’t blame him, Rory clearly knew she had feelings for Jess but continued dragging Dean along because Jess was otherwise occupied. Though you hated what Jess had done to you, leaving you feeling used, there was a part of you that still wanted him back. 

Maybe that was the reason for this quite frankly insane plan you and Dean had come up with. The two of you had only spoken a hand full of times, Rory wasn’t exactly your biggest fan to begin with and then Jess began hating Dean, there just hadn’t been a good opportunity since he came to the small town of Stars Hollow but now there was. The two of you had pretty much all your classes together and you watched as Dean came in, looking about as good as you felt. The lack of sleep was clearly visible and he just radiated sadness, the same went for you though. Along with the sadness and hurt both of you felt, there was also a deep feeling of embarrassment, both break ups had been rather public and of course gossip spread like wild fire in a town like this. 

“Hey Y/N.” Dean had shocked you one day by joining you under a shaded tree that hid you rather well from the rest of the school. Dean had smiled at you confused expression before asking if he could join you.

“Hi Dean, um, yeah, sure.” You’d manage to reply, honestly confused as to why the ex-boyfriend of your ex-boyfriends girlfriend would want to talk to you.

“Listen, I just wanted to say I know how you’re feeling. It sucks, right, but if you ever need to talk to someone, someone who won’t use it as gossip and have it around the town within the hour then just know I’m here.”

That’s how it started. The sincerity in his voice had you believing him and it wasn’t long before you two were sat under the tree hashing out the details.

“Hold on, you want us to fake date?” You’d asked when he brought the idea up one break time.

“I just think that it’ll get some sort of reaction out of them, make them jealous. I mean Rory doesn’t like you and Jess, well we all know how he feels about me.” Dean said with a sarcastic laugh, causing you to smile. “Say no if you want to but I don’t know, it could be interesting.”

“Dean,” You began, upon first hearing the idea it was absurd but the more you thought about how much Jess and Rory had hurt you two, the more it seemed like a good idea. “Let me think about it?” You asked causing him to nod immediately.

“Of course, please take your time. I’ll see you later, Y/N.” You watched as Dean walked away with a slight frown on your face as you thought about what he had said.

-

-

-

It was a week before you’d talk to Dean again. You hadn’t planned on talking to him but you saw him through the window of Luke’s alone and made up your mind then and there.

“May I join you?” You asked as you made your way over to him. Dean looked up from the work he was doing in surprise, only to smile a moment later.

“Y/N! Yes, please have a seat.” He said, gesturing to the seat opposite him. 

“What can I get for you, Y/N?” Luke asked before you had the chance to open your mouth. You quickly ordered your regular and turned back to Dean as Luke left.

“So, what’s up?” He asked, fiddling with his pen.

“I’ll be your fake girlfriend.” You told him quietly with a grin. He looked at you for a moment as if working out whether you were being honest before he grinned back at you. 

Luke brought you your drink and quickly filled Dean’s up before leaving and before you knew it two and a half hours had passed and you and Dean were still sat in the diner, getting to know one another. 

It struck you that Jess had never bothered to get to know the little things about you that Dean was asking about but you pushed that thought from your mind as quickly as it had come.

“We’ll I should probably go, I didn’t mean to stay this long and I still have that English homework to get done.” You groaned causing Dean to laugh.

“C’mon, I’ll walk you out. I’ve got work anyway.” 

As luck would have it as the two of you rounded the corner, Lorelai and Rory nearly walked into you. Whilst Lorelai apologised, you and Dean doing the same, Rory just looked between you and Dean before settling on a glare.

“Well that went well.” You laughed once the pair walked into Luke’s, Dean laughing along with you. “I’ll see you tomorrow then, yeah?” You asked.

“Yeah. You want to meet up here and get some coffee before school?” 

“I’d love to.” With that the two of you went your separate ways not noticing the glare Rory was giving you from the diner.

-

-

-

“Did you hear the news?” Babette asked Lorelai one morning, two weeks after you and Dean agreed to fake date.

“No, what news?” Lorelai asked as she leaned against the counter at Luke’s. Luke listened too though not making it obvious and Jess glanced over from were he was talking to Rory.

“Well,” Babette started with a hesitant look towards the young couple, “I heard from Patty, who heard from Joe, who heard from Tom, that Dean and Y/N are dating! I mean can you believe it!” She exclaimed, not noticing the dark look on Rory’s face and the eye roll and mask of indifference on Jess’.

“Wait, Y/N and Dean? As in Rory’s ex boyfriend and Jess’ ex girlfriend?” Lorelai asked, shock clear in her voice.

“Oh my thoughts exactly, doll, I mean who’d have thought it? Anyway, I gotta go, Morey’s expecting me back any moment. See you soon sugars.” And with that Babette left, leaving everyone with different thoughts running through their heads.

-

-

-

Dean and you were sat in Luke’s, both noting how Jess glared at the two of you and pointedly ignored your table. Luke rolled his eyes before taking your orders.

Dean had told you on your walk over to Luke’s about how Rory had shown up at his window, how her apology seemed self-centred and how Rory said she loved him. Dean had sent her away, furious at her for even showing up.

You couldn’t blame him for his anger, especially not when Jess had cornered you when you were leaving the market spouting all the right words of how much he liked you, how Dean was no good. 

It was safe to say the urge to slap him was real. How dare he say Dean was no good for you when he ditched you the moment Rory left Dean. 

“So, were are we up to?” Dean asked as he moved his chair closer to you, neither of you noticing Rory, Lorelai and Sookie entering the diner and sitting at the opposite end.

“Ugh math.” You told him with a grimace. The two of you were taking this extra time together to help each other with school work, focusing on topics the other wasn’t so good at and teaching it until it made sense.

You had helped Dean with English and science, helping to come up with easy ways to memorise important passages of texts or formulas. Whereas Dean was helping you with math, the one subject that you needed to raise your grade in order to even have a chance at the colleges you were looking at. 

Dean had confided in you he hadn’t thought much about college, not knowing what he wanted to do. You in turn helped him research different colleges and he eventually found a few with courses that interested him. Now that you both had a vague idea of what you wanted it was easy to set targets and help each other.

“C’mon now,” Dean laughed, wrapping his arm around you as you pressed your forehead to his shoulder with a groan, “you’re getting better.” 

“No I’m not. I’m gonna fail, there’s no hope.” You pouted overdramatically causing him to laugh louder before pressing a subconscious kiss to your head.

“No, you won’t. You wouldn’t let me fail and I won’t let you.” He told you, voice hard with determination. 

“Fine, fine. Let the torture begin.” You groaned but shot him a grin. 

As the two of you pulled your books out you missed the way Rory and Jess glared at you.

“I can’t keep up, one minute your falling all over Jess whilst you were with the nicest guy ever and now that you’re with Jess you want Dean back.” Lorelai said with an eye roll as she watched Rory.

“What?” Rory jumped, finally looking away from you two. “I don’t want him back, it’s just, I don’t know.” She finished weakly, slumping down in her seat.

“You have to pick, Rory. I told you that when you were dating Dean and you picked Jess.” 

“He broke up with me!” Rory protested weakly.

“Because he saw the way you were with Jess, he knew you liked him and no matter how hard that boy tried he knew he couldn’t carry on like that.” Lorelai argued, knowing she was right.

Rory just rolled her eyes before grabbing her bag and walking out of Luke’s. You and Dean were oblivious to the whole thing as you sat close enough together that your foreheads were touching with Dean praising you with every bit of progress you’d made.

-

-

-

It wasn’t long before exam season finally rolled around and you were stressed. Every free moment was spent in either your bedroom, Luke’s diner, the library or Dean’s bedroom studying.

Currently you were on the floor of Dean’s bedroom, books and loose sheets of paper surrounded you. Dean was in the same position on his bed. It wasn’t long before you let out a loud groan, throwing your head back against the bed and rubbing your eyes. 

Dean climbed off the bed before sitting next to you. He wrapped his arm around you, pulling you close with concern in his eyes. 

“You ok?” He asked softly, frowning as you shook your head whilst mumbling about failing into his shoulder.

“Hey, you’re not going to fail, ok, you know this. Watch,” he said, whilst pulling away from you and searching through your pile of paper before finding a deck of study cards. “Ok, the ratification of the eighteenth amendment led to what?" Dean asked.

“It led to a ban on the manufacturer and sale of the alcoholic beverages.” You said, biting you lip before grinning at Dean’s nod.

“Perfect!” He exclaimed with his own grin, “Which president signed the Antipoverty Act into law?” He questioned, watching as your smile grew.

“Lyndon B Johnson.” You answered confidently, causing him to laugh.

“See you know it!” He told you, “Ok, so if A equals 1,2,3 and B equals 3,4,5, how many sections are in the intersection of A and B?” He asked. You bite your lip as the question ran through your head.

“One?” You questioned and upon seeing him nod you relaxed slightly. 

“Good!” He praised and that’s how the next half hour was spent.

“Ok, my turn to question you!” You told him as you reached up for his set of cards. 

“Ok, so within a specified period, an increase in atomic number is usually accompanied by what?" Watching as Dean squinted, his head titling slightly to the right in concentration, you couldn’t help but think of how cute he looked. Your eyes widened at the thought, shaking your head just as Dean answered.

‘A decrease in atomic radius and an increase in electronegativity.” He replied nervously.

“Yes!” You beamed up at him and he couldn’t resist smiling back. 

The two of you quizzed each other until you feel asleep. You with your head on Dean’s shoulder, Dean with his head resting on yours.

-

-

-

The morning after the two of you had woken up late and quickly rushed to get ready. You had no other clothes and had no time to run home so ended up in yesterdays jeans and one of Dean’s shirts that, whilst tucked in still looked ridiculously big. Though Dean admitted, if only to himself, that he liked the look of you in his clothes.

The pair of you rushed to the school, skipping your morning drinks at Luke’s for the first time since you started ‘dating’. Everyone congregated outside of the hall to sit the first exam of the day; Math. 

Dean watched from his positon of leaning against the wall as you paced back and forth, muttering different equations to yourself. It wasn’t long before he pulled you into his arms, you relaxing slightly with a second thought.

“You got this.” He told you sincerely, leaning down to kiss your forehead. 

“I hope you’re right.” You whispered as you were let into the hall.

“Good luck.” You told him, leaning up on your toes to kiss his cheek.

“You too, Y/N/N.” 

-  
-

-

Two exams down and you were sat outside on a bench waiting for Dean, whilst your math exam was at the same time, he had an English exam that started later than yours.

You sat with your laptop, finishing the last of your college application letters and had them sent off. You’d applied for two ivy league schools just on the off chance you did get accepted, those being Yale and Princeton, though you had also applied to Stanford, NYU, Michigan and Chicago. It was a relief knowing that they were sent off and now all you had to worry about was the exams themselves.

“Hey there.” You leaned your head back to see Dean smiling down at you, looking relaxed for the first time all day. 

“Hey! How was the exam?” You asked, knowing how much he was dreading it. 

“Honestly, I think it went pretty well but that’s only thanks to all the extra help I’ve been getting.” He grinned at you, leaning forward to peck your lips. “Whatcha doing?” Dean asked leaning his head on yours.

“I just finished sending all my college applications off.” You said letting out a breath of relief.

“I need to send mine off tonight.” He told you as he stood up, holding his hand out for you which you happily took and he led you to the diner.

“Are you working tonight?” You asked him, frowning slightly when he nodded. 

“Yeah but Taylor’s letting me go early because I told him I need to study.” The conversation drifted off into talk of the science and lit exams tomorrow before Dean was leaving for work, leaning over and kissing you first.

“What are you doing with him?” Jess asked as he sat himself in the chair Dean had been occupying.

“Excuse me?” You asked, lifting the mug to your mouth. Luke watched from the counter, ready to step in if Jess upset you.

“I mean, Dean, seriously? You could do so much better.” He told you, slouched in the chair like he didn’t care.

“What’s going on there?” Lorelai asked Luke as she approached the counter.

“Dean just left and now Jess is bothering her.” Luke summed up as he poured her a cup of coffee.  
“Really?” You asked, voice loud enough for everyone in the diner to hear. “You mean like you, the guy who ditched me the moment Rory and Dean split up? Yeah I’m sure Dean’s a real downgrade. I gotta tell you though being with Dean has been so much better than being with you. If you ask me, I think Gilmore’s the one who got the downgrade.” With that you stood, scooping your laptop into your hands and walked out of the diner with your head held high.

It was safe to say your outburst was the talk of the town that evening.

-

-

-

“What a jerk.” Dean replied once you saw him the next day.

“Right.” You said. The two of you were sat on a patch of grass in his garden leaning against one another. One thing that had bothered you from your meeting with Jess yesterday was how you meant every word; being with Dean was so much better. At some point the kisses and handholding for the public had turned into second nature responses, half the time you forgot you weren’t really dating.

“Anyway it’s fine. Honestly, I was over him a long time ago.” You said causing Dean to smile. “Did you send your applications in?” Dean told you he had and told you which colleges he had decided on, most of them were community colleges but one caught your attention.

“Stanford!” You exclaimed. “You applied for Stanford! Dean, that’s amazing.” You had known Dean had been debating it but eventually decided against it due to him doubting himself despite your protesting and praising. The fact that he had even decided to apply was big.

“Okay, okay, calm down.” He laughed, “I haven’t got in yet. Hell, I doubt I will but it didn’t hurt to apply and-” You cut Dean off with a kiss before pulling back with a grin.

“It’s amazing Dean, they’ll be foolish to turn you down.” You told him, causing him to pull you in for another kiss.

It didn’t occur to either of you that no one was around to see it.

-

-

-

“I got them.” You said into your phone. Currently you were walking to the town centre with six college admission letters in your hand. Dean and you had decided to wait until you both had all your letters until opening them.

“Me too, I’ll meet you under the gazebo.” Dean said before the two of you hung up. 

You were so anxious. The fate of your future laid in your hands, literally. By the time you got to the gazebo you were pale and shaking.

“Hey, hey, sit down.” Dean said, taking your free hand and pulling you to sit on the bench. He helped you breath properly before talking to you.

“Whatever happens you’ll be fine, I promise.” He told you. You nodded at him before taking a deep breath.

“Ready?” You asked.

“Ready.” He confirmed.

The first letter came from Princeton, it was a rejection letter. Though you were expecting it, not really wanting the Ivy league ones but applying just to see. It disheartened you but you set it aside.

Dean opened his and saw he was accepted into Southern Connecticut State. 

The second letter came from NYU and you grinned once you saw the acceptance. 

Dean’s second letter was also an acceptance.

The third and fourth informed you both that you had gotten into the colleges.

You opened the fifth letter and were shocked to find you had been accepted into Yale. Dean grinned at you as you stared in disbelief. Realistically you knew you weren’t picking that college, purely on financial matters alone but also you weren’t an ivy league school person.

Dean and you both had one envelope left; Stanford.

The two of you stared in shock as you read you had both been offered a full ride scholarship.

“Y/N!” Dean exclaimed pulling you up and into a tight hug. Your arms wrapped around him as you took in the words; the college you had most wanted had not only accepted you but given you a full ride.

You were pulled out of your thoughts as you felt Dean kiss you passionately, when he pulled away the two of you were panting as he leaned his forehead against yours.

“Screw this, Y/N.” He said pulling away causing you to frown. “I can’t do this fake dating anymore, somewhere along the way I fell in love with you. Will you be my girlfriend? For real this time?” He asked with a slight laugh, causing you to grin and nod, an exclamation of yes leaving your mouth before Dean pulled you into another kiss.

“I love you too.” You whispered as he pulled back.

Dean just grinned at you before kissing you again, loving that he could now knowing his feelings were reciprocated and it wasn’t just for show.

-

-

The two of you had found an apartment not far from the campus but far enough away that it was still considerably cheap. It wasn’t the greatest place but it was yours and Dean’s home. You took a job in the college library and Dean picked up a job in the cafeteria. 

The two of you settled into living together rather well, obviously there were a few arguments here and there but moving out of the small gossiping town of Stars Hollow had done you both the world of good.

Dean was studying engineering at an advanced level and you were finally studying what you wanted and loved it.

The two of you had never been happier and even though it was all thanks to your ex’s and Dean’s fake dating idea, you wouldn’t have changed it for the world.


	2. I'm So Glad This is Real

**Summary for the Chapter:**

> Someone requested (on Tumblr) that I do a part two in which we see flashes of Dean x Readers life set during a year in the life. 
> 
> Enjoy!

It had been a long, long, road to get to where you were now but somehow the two of you had done it together. Sure there had been fights, what couple didn’t argue, and there had been a few close calls, though one time you had broke up for a week before realising how foolish the both of you had been.

_ “Honestly Dean! We’ve been dating since we were seventeen, you really don’t trust me?” You yelled at him from one side of the room. _

_ “Of course I trust you, Y/N!” Dean yelled back, just as frustrated. It was finals week during your first year of Stanford. The stress was higher than ever and you had joined forces with another classmate to study and Dean had read too much into it. Looking back it was the stress of everything building up to this but in the moment it was impossible to think logically. “But you said it yourself, we’ve been together since we were kids! You can’t blame me for thinking you’d want to explore something else.” Hearing those words you glared at Dean. _

_ “Maybe it’s not me who wants to explore.” You said, voice low and cold as you shouldered your way past him. He gently took your wrist in his hand but let go when you pulled away. _

_ “Y/N, you know that’s not what I want or meant. I love you for God sake.” He pleaded as you touched the door handled. _

_ “Don’t call me” You said before walking out the door and crashing at your friends dorm for the week. _

_ After finals you and Dean finally met up, talking and laughing and apologising. _

Yeah, you thought, safe to say college was a stressful time.

The two of you visited Stars Hollow during most holidays but during your third year at college the pair of you decided to try hosting Christmas. Clara and Dean’s parents came whereas yours had to travel to see extended family, something you weren’t too worried about missing.

_ “Dean!” You laughed as you saw the man standing over the burning vegetables. “What did you even do?” _

_ “Stop laughing and help me.” Dean pouted, looking hopelessly down at the broccoli that definitely wasn’t green anymore, nor were the carrots orange. _

_ “Hand it over, sugar. You focus on the mash.” You couldn’t help but laugh again at the weary look Dean gave between you and the potatoes waiting to be mashed. “C’mon, even you can mash some potatoes.” _

_ You restarted the vegetables, missing the loving smile Dean gave you from his corner of the kitchen as he watched you dance around the kitchen with the cheesy Christmas music blaring from the speaker. _

_ He knew then and there he’d be the biggest idiot ever to lose you _ .

Overtime the two of you had gotten better at hosting parties for different occasions, Dean even eventually learned to cook vegetables without burning them, though the one time he was left in charge of the turkey, well lets just say it’s a good thing you had the foresight to buy a spare.

Graduating from Stanford was something to be proud of in itself. Graduating top of your class was a whole other accomplishment. Dean had hugged you close as he whispered praises and kind words into your hair, kissing you softly and taking you out for one of your favourite dates that you’d ever been on.

Well you definitely thought nothing could beat it at the time but that’s a memory for later.

_ “I am so proud of you, sweetheart.” Dean whispered as he held you to his chest were you’d sagged out of shock. You were a hard worker but never once did you think you’d be the best in your classes at Stanford! _

_ Dean had told you he was taking you out to the new restaurant that had opened not too far from your home. You were beyond excited as you slipped on one of your nicest outfits. _

_ “You look gorgeous.” Dean said as he came into the bedroom, sliding his arms around your waist. _

_ “Yeah?” You said turning around in his hold, looking him up and down. “Don’t look too bad yourself, sugar.” He grinned down at you before pulling you in for a soft kiss. _

_ “You ready?” He asked and you nodded, kissing him once more before letting him pull you out of the apartment and towards the car. _

There was one night you remember clearer than most. You’d been rejected for yet another job, hating the one you were at now but having to persevere until another opportunity came along.

_ You walked through the door before closing it and just leaning against it, letting your head fall back with a loud thud. Tears that you desperately didn’t want to fall welled up in your eyes as Dean popped his head around the living room door. _

_ “Another rough day?” He asked you, sympathy clear in his eyes. _

_ You just nodded tiredly from where you were. Dean sighed before standing up and walking over to you, taking you into his arms and kissing your forehead softly. _

_ “C’mere baby, I got something that’ll cheer you up.” He told you causing you to look up at him questioningly. His only response was to kiss you before pulling you into the living room, stopping when you paused in the hallway. _

_ The room was covered in blankets and throws, fairy lights were visible from the outside and there was a small opening being held by a pillow in which you could see the TV on with your favourite film ready to play and your favourite comfort food lay waiting for you. _

_ “Dean.” You choked out, a few tears leaving your eyes as you turned to look at him. _

_ “I thought you could use a break.” He told you quietly. You quickly threw yours arms around his neck, standing slightly on your toes to do so. Dean smiled brightly as he rested his head on yours before prompting you into the fort. _

_ You two spent the rest of the night watching each others favourite films again, laughing and smiling the entire time. _

It had taken awhile but both you and Dean were finally doing what you loved. You had somehow landed your dream job when you ended up at a party for your old job and accidentally met the boss, wowing him with your knowledge. Dean was working as a mechanic working on vintage cars, it would be a few years but eventually the boss would hand the business over to his best employee.

The best date came after the two of you had moved into a house together, leaving behind the apartment that had become your home and into an actual house. Dean had told you to meet him at the park at six pm, the park was quiet anyway but by then it was practically empty. You dressed appropriately as the autumn chill set in and made your way down to meet Dean.

_ You gasped as you took in the fairy lights hung from the tress and the picnic basket that Dean was sat next to. Upon hearing your gasp Dean looked up and smiled at you. _

_ “Y/N!” He beamed, standing up and kissing you in greeting. _

_ “Hi baby, what’s this?” You asked as he led you to the blanket. You both sat and Dean started laying food out for the two of you. _

_ “Am I not allowed to take the girl I love out on a date?” He asked sarcastically with a grin. _

_ The two of you laughed. The food was ate but you noticed over the course of the meal Dean had become more nervous. Once you were finished you couldn’t help but ask if everything was alright. _

_ “Yeah, everything’s perfect.” He told you as he wiped his hands on his pants. “It’s just, I love you. We’ve been together for eight years, you’ve been there to help me at Stanford, sat with me when I felt like the world was going to swallow me up and honestly, baby, I can’t imagine the rest of my life without you. I try and it’s just impossible. I love you so much and well I guess what I’m trying to say, or well ask, is will you marry me?” _

_ You were shocked speechless for a moment or two before Dean prompted you to speak.  _

_ Tackling him to the floor from your seated position you let tears of joy roll down your face as you chanted ‘yes.’ You heard Dean laughing, felt his own tears fall down his face before he pulled you back enough to were he could see you. _

_ “Is that a yes that?” He asked, smiling cheekily despite the tears. _

_ “Yes, you idiot.” You laughed, pulling him into a deep kiss. _

“Hey Y/N, you ready to leave?” You heard your fiancé call out as he walked into the house.

“Come help me please?” You yelled back at him from upstairs. Dean smiled as he followed the sound of your voice, raising an eyebrow as he saw you sat on top of a suite case trying to zip it shut.

“Y/N, we’re going for a weekend!” Dean laughed as he pulled you up off the suitcase.

“And?” You asked. Kissing him in greeting before looking back towards the case.

“And do you really need all this stuff?” You looked up and saw him glancing at your case and the overnight bag.

“Yes, I do, now are you going to help me shut it or are you going to question me?”

“Both.” He laughed. It took more tries than either of you were bothered to count but eventually the case was closed and the two of you were in Dean’s car and on your way to Stars Hollow.

It was a long drive but finally the two of you pulled up at Dean’s parents house. Greetings were gave but it wasn’t long before everyone retired to bed, the drive exhausting both of you.

You and Dean were cuddled up in his childhood bed, tucked close together whispering quiet words between you and it wasn’t long until you both drifted off to sleep.

-

-

-

Dean had left to go to the store and you had taken the opportunity to go to Luke’s. Memories bombarded you as you walked through the door and you couldn’t help but smile at them all, from agreeing to fake date Dean to arguing with Jess.

“Y/N!” Luke greeted as you walked to the counter.

“Hi Luke.” You smiled and watched his eyes flicker to the ring on your finger that definitely wasn’t there during your last visit.

“So, he finally asked, huh?” Was all Luke said. You never noticed Lorelai sitting a few seats down at the counter looking over in interest.

“He finally asked.” You confirmed, Luke smiling at the love struck look on your face.

“Good, bout time he popped that question. Know any details yet?” He asked sliding your drinks over.

“Thanks. And no, honestly work has been stressful, the last thing I want to do is plan a wedding.” You groaned the smile never leaving your face.

“Yeah, can’t say I blame you.” Luke chuckled before excusing himself to see to another customer.

“Congratulations.” You looked in surprise to see Lorelai smiling softly at you.

“Oh, thank you.” You smiled back.

“Can I see it?” She asked gesturing to the ring and you showed her. The two of you immediately going into how Dean had asked and gushing over it, Luke smiling over at the girl he’d known since she was as tall as his knees.

-

-

-

Dean rounded the corner not paying much attention as he did before he crashed into somebody. He quickly reached out to steady them.

“Oh sorry.” He heard the voice of the girl who he hadn’t seen for years. Since they’d both left for college it was rare for them to be in Stars Hollow at the same time.

“Hey.” He greeted as he took in Rory, the pair hugging as Rory told him how good it was to see him.

“What are you doing in Stars Hollow?” She asked him.

“I’m just visiting my parents for the weekend.” He smiled.

“That’s nice.”

“It’s very nice,” Dean began “we’re actually here because Y/N and I got engaged.” He told her with the same grin he’d always had when talking about you.

“You’re engaged? Dean, congratulations, I’m so happy for you.” She exclaimed, drawing him in for another hug.

“Yeah, thank you.” He laughed.

“How is Y/N?”

“She’s great, she got the job she’s wanted for so long. They’re thinking of promoting her again and yeah, she’s, she’s really amazing.” Dean told her.

“I’m really happy for you, Dean.” The pair smiled at each other for a moment before speaking about the rest of their family, Rory asking about Clara and Dean asking about Lorelai.

“It’s her first love, it’ll probably…” Rory trailed off and the two stood in an awkward silence for less than a moment before Dean spoke.

“Yeah, I know.” Despite the awkwardness he still smiled at her. She was his first love after all and without her who knows where he and Y/N would be now.

“How’re you doing?” Dean asked, not wanting to dwell on the past.

“Me?” She asked, not waiting for an answer, “I’m doing ok.”

“Just ok?” Dean asked, concern in his voice.

“Well things are changing for me at the moment, I’m still trying to figure it out. I’m writing a book.” She announced.

“Well, you’ve read em all so what else you gonna do?” He asked with a chuckle.

“It’s actually about my mom and me and our life.” She nodded at Dean’s questioning response.

“Can I put you in it?” Rory asked. Dean looked confused for a moment, not knowing how to respond.

“Um…” He trailed off and Rory cut in before he could make a decision.

“I mean I’m changing the name to protect the guilty but you’d know it’s you.” She spoke, hoping the man she had once loved would agree.

“Uhm, I uh, I don’t know. What’re you gonna say?” He asked her, not shutting the idea down straight away but not fully loving the idea. Who knows what Rory could write about him.

“That you were the greatest boyfriend alive.” Was the first thing you heard Rory say as you walked into Doose’s with two take out cups, you could see Dean from over the shelves and debated joining them before deciding it was best to just let them talk. She wasn’t wrong about Dean being the greatest boyfriend though, she just hadn’t appreciated it enough at the time, not that you were complaining, you thought looking down at the ring on your finger before pressing your hand to your stomach.

“That you were um, generous and protective and kind and strong and as much as I wish we'd met when I was older and more mature, I know that if I hadn't had you with met when I did I wouldn’t be the person I am today. That you taught me what safe feels like.” Rory’s words were honest and you found yourself relating, safe was wherever Dean was, home was wherever Dean was.

“Ok.” Was Dean’s only response and though you wanted to go to him you knew he needed this.

“And that you had a disturbing obsession with Lord of the Rings-” Boy did you know that all too well, “that you did a terrible Sméagol impression…” Here she was cut off by a laughing Dean, in his defence the impression had gotten slightly better over the years.

“It was not terrible. It was pretty damn good. There were hand gestures.” Like you said, only slightly better.

“I know, I remember. I remember it all really well.” She laughed with him.

“Good luck with the book.” Dean told her softly.

“Thank you.”

“Dean!” She called. “Corn-starch.”

“Pay for it this time.” Dean chuckled before turning away and spotting you. You smiled at him and held a cup in his direction.

“Hey.” He kissed you in greeting and the two of you headed to the gazebo before taking a seat on the steps.

“She’s writing a book?” You confirmed.

“A book.” Dean nodded, playing with the cup in his hands.

“Well she got one thing right. You are the best boyfriend alive.” You laughed, Dean quickly leaning over and kissing you.

“So you want some news?” You asked staring ahead as the two of you stood up.

“News?” Dean asked in confusion. You turned to look at him, smiling nervously and playing with one of his hands.

“You’re gonna be a dad.” It took a few moments for the words to sink in before a grin broke out on the mans face. He took you into his arms and spun you around before placing you down and cupping your face with one hand.

“You’re pregnant?” He asked.

“I’m pregnant.” You confirmed and he pulled you in for a kiss, deepening it quickly. You wrapped you arms around his neck and when the two of you pulled back panting and grinning, you knew this was it, you couldn’t think of any other way you wanted to spend your lives.

**Notes for the Chapter:**

> As always feel free to request in the comments or through tumblr on https://multi-fandom-imagines-x.tumblr.com/
> 
> Thanks for reading!

**Author's Note:**

> Thanks for reading. 
> 
> Again feel free to request something, I'm on lockdown like the rest of you so I have nothing else to do now that uni has finished.
> 
> You can request with your own prompts or use my prompt lists. 
> 
> https://multi-fandom-imagines-x.tumblr.com/


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